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Chiddy’s Cheesesteaks opens in West Islip; chain now counts three Long Island eateries

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The West Islip community can now indulge in authentic Philly cheesesteaks right in their own backyard. 

Chiddy’s Cheesesteaks unveiled its third shop back in January at 510 Union Blvd., and have been pumping out the Philadelphia staple, along with their signature sandwiches, South of the Border items and other menu items. 

Mike Chidester ventured into the cheesesteak business after almost 30 years in the corporate world, having worked in management for such big companies as Coca-Cola and IBM. He said he had long been interested in owning a sandwich shop, and it just so happened his nickname made for a catchy business title.

“I’ve been a cheesesteak fanatic all my life. I used to vacation on the Jersey Shore, and that’s when my love for cheesesteaks came to be,” Chidester said. “Chiddy is actually my family nickname, so a lot of people didn’t know I had a first name, Mike. They just called me Chiddy.” 

At the time, hot dog trucks were the most common type of food truck on Long Island. Chidester said he decided to explore the cheesesteak concept further, adding that he felt there was a “void” in authentic Philly cheesesteaks across the island. 

So, he merged the two concepts and launched Chiddy’s Cheesesteaks food truck in 2014 in the Market shopping center in Bay Shore (1851 Sunrise Highway). 

Chiddy’s second food truck kicked off in 2017 and not long after, Chiddy’s Cheesesteaks debuted its first physical storefronts in Farmingdale and Commack, six months apart in 2018. 

Chidester said instead of continuing to put more food trucks on the road, he decided the future of the company lay in brick-and-mortar restaurants.  

The wheels really started turning for the business during a discussion over beers between Chidester and two friends, Evan Deitch and Daron Benbenisti. 

“We joined forces, and once we decided we really wanted to explore this opportunity, I think that day we jumped in the car and started looking for spots,” Chidester said.

Franchising opportunity

Once Chiddy’s gained popularity, the team looked into franchising in 2020 — at the height of the COVID-19 pandemic. 

The restaurant’s ability to provide quality takeout benefited them during their temporary shutdown and allowed them to continue to grow the brand. 

Their first franchisee was Joe Archipolo, a former employee who had worked his way up since he began working at Chiddy’s as a teen. He bought the Commack location in November 2021.

“He’s thriving and that helped us to be able to finance the new West Islip location, and continue to grow,” Chidester said. “We believe we could be in every other neighborhood on Long Island.” 

Fun and vibrant decor

The West Islip Chiddy’s stays in touch with the food truck theme through its fast-casual structure and bright interior décor. In addition to the food truck mural at the register, vintage rock n’roll band posters also line one wall. A giant menu is featured on another wall. 

Chidester said they brought traditional Philly ingredients into their recipes, which includes sourcing straight from Pennsylvania’s largest city.

Chiddy’s menu consists of “good mood food,” including empanadas, quesadillas, tacos, nachos and chili cheese dogs. 

“The whole concept of #FoodTruckLife — we try to keep it casual, high-energy, dealing with the fast-pace [environment], while still having fun,” Chidester said. “We built really good teams at all of our locations.” 

Early favorites

Among the eatery’s crowd-pleasers is the uber popular Chiddy’s Signature, which is ribeye steak, onions, peppers, mushrooms, provolone and cheese whiz. Another favorite is the “Build-Your-Own Cheesesteaks” option.

At West Islip, Chidester said, everything is selling. And he added that as far as expansion goes, it’s full steam ahead.

He said he and Chiddy’s other two founders won’t be “satisfied” until they get to where the Chiddy’s Cheesesteak brand can take them, which can potentially be anywhere on Long Island or the country.

“Every now and then when the three of us sit down and talk, I try to catch us and say ‘We ought to sit back and see what we’ve done in a matter of three years, and amid the pandemic. We’ve opened three locations in a very challenging environment ,and all three locations are thriving.”